An improved procedure for the asymmetric aldol reaction of the titanium enolate of an N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one |
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| Institution: | 1. Organization for the Strategic Coordination of Research and Intellectual Properties, Meiji University, Kawasaki 214-8571, Japan;2. Department of Applied Chemistry, Meiji University, Kawasaki 214-8571, Japan |
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| Abstract: | The direct formation of the titanium enolate of N3-propionyl-3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-one has been achieved through complexation with titanium tetrachloride at 25°C, followed by deprotonation with triethylamine (?78 to 25°C). The preformed titanium enolate has been reacted with D2O/DCl to afford deuterated derivative 6 and also reacted with a series of aromatic and aliphatic aldehydes affording aldol adducts 4a–f with crude diastereoselectivities ranging from 8:1 to 38:1. |
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